Literature DB >> 27529614

Bifunctional-Phosphine-Catalyzed Sequential Annulations of Allenoates and Ketimines: Construction of Functionalized Poly-heterocycle Rings.

Erqing Li1, Hongxing Jin1, Penghao Jia1, Xuelin Dong1, You Huang2,3.   

Abstract

A highly stereoselective sequential annulation reaction between γ-substituted allenoates and ketimines was reported. By using bifunctional N-acyl aminophosphine catalysts, poly-heterocycle rings were obtained with high stereocontrol in good to excellent yields. The desired products have four contiguous stereogenic centers (one quaternary and three tertiary carbon centers), and only one isomer was obtained in all reactions.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  allenoates; bifunctional phosphines; domino reaction; poly-heterocycle rings; sequential annulations

Year:  2016        PMID： 27529614     DOI： 10.1002/anie.201605189

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


  6 in total

Review 1.  Phosphine Organocatalysis.

Authors:  Hongchao Guo; Yi Chiao Fan; Zhanhu Sun; Yang Wu; Ohyun Kwon
Journal:  Chem Rev       Date:  2018-09-27       Impact factor: 60.622

2.  Phosphine-catalyzed [5+1] annulation of δ-sulfonamido-substituted enones with N-sulfonylimines: a facile synthesis of tetrahydropyridines.

Authors:  Leijie Zhou; Chunhao Yuan; Yuan Zeng; Honglei Liu; Chang Wang; Xing Gao; Qijun Wang; Cheng Zhang; Hongchao Guo
Journal:  Chem Sci       Date:  2018-01-05       Impact factor: 9.825

3.  Catalytic Enantiodivergent Michael Addition by Subtle Adjustment of Achiral Amino Moiety of Dipeptide Phosphines.

Authors:  Huamin Wang; Xiuzheng Li; Youshao Tu; Junliang Zhang
Journal:  iScience       Date:  2020-05-06

4.  Design, synthesis and application of a new type of bifunctional Le-Phos in highly enantioselective γ-addition reactions of N-centered nucleophiles to allenoates.

Authors:  Haile Qiu; Xiaofeng Chen; Junliang Zhang
Journal:  Chem Sci       Date:  2019-09-03       Impact factor: 9.825

5.  Phosphine-catalyzed divergent domino processes between γ-substituted allenoates and carbonyl-activated alkenes.

Authors:  Mingyue Wu; Zhaobin Han; Huanzhen Ni; Nengzhong Wang; Kuiling Ding; Yixin Lu
Journal:  Chem Sci       Date:  2022-02-11       Impact factor: 9.825

6.  Elucidating the mechanism and origins of selectivity on catalyst-dependent cyclization reactions to form polycyclic indolines from a theoretical study.

Authors:  Yan Zhang; Yongsheng Yang; Ying Xue
Journal:  RSC Adv       Date:  2021-06-09       Impact factor: 4.036
  6 in total

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